Water → HCID 67524617, compound

HRID 517816Notes

Reaction equation

HRID 517816 reaction equation
[H-].[Na+].[CH:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[Cl:10][C:11]1[N:15]2[N:16]=[C:17](Cl)[CH:18]=[CH:19][C:14]2=[N:13][N:12]=1.O>O1CCCC1>[Cl:10][C:11]1[N:15]2[N:16]=[C:17]([O:9][CH:3]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)[CH:18]=[CH:19][C:14]2=[N:13][N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 14823463,6-Dichloro[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 67524617HCID 67524617, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

106 mg of sodium hydride at 60% in oil are added to a solution of 530 mg of cyclohexanol in 5 cm3 of tetrahydrofuran at 0° C. under argon. After stirring for 15 min, 500 mg of 3,6-dichloro[1,2,4]triazolo[4,3-b]pyridazine (commercial) are added. The brown suspension is stirred, allowing the temperature to return gradually to 20° C. for 24 h. The reaction medium is poured into water and the mixture is extracted with ethyl acetate. After concentration to dryness under vacuum, a brown powder is obtained, which is washed with ether. The filtrate is concentrated to dryness and the oily yellow residue is chromatographed on Biotage Quad 12/25 (KP-SIL, 60 A; 32-63 μm), elution being carried out with a gradient of 100% dichloromethane to 95:5 dichloromethane/methanol. 184 mg of 3-chloro-6-(cyclohexyloxy)[1,2,4]-triazolo[4,3-b]pyridazine are thus obtained in the form of a white powder, the characteristics of which are as follows:

Workup

  1. stirringThe brown suspension is stirred
  2. waitto return gradually to 20° C. for 24 h
  3. extractionthe mixture is extracted with ethyl acetate
  4. concentrationAfter concentration to dryness under vacuum
  5. customa brown powder is obtained
  6. washwhich is washed with ether
  7. concentrationThe filtrate is concentrated to dryness
  8. customthe oily yellow residue is chromatographed on Biotage Quad 12/25 (KP-SIL, 60 A
  9. wash32-63 μm), elution

Sources & evidence

ORD record
ord-08dda06f6e0a4ecc8265a56383cdc1b0
Source dataset
uspto-grants-2015_08
Patent number
US09115134B2

Reaction notes

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